The Tranny Chaser Chaser

June 22, 2011

I’m no stranger to the walk of shame, but this is the first morning I’ve ridden the R train into Manhattan with metallic blue eye shadow smeared across the upper third of my face like a sloppy Warhol silkscreen. I’ve spent the prior evening at a bacchanal called Eden Underground: a sex party for transsexuals and their admirers in Park Slope that just rang in its one-year anniversary. What brought me to the polymorphously perverse bi-monthly Friday night was a search for gender identity’s Yeti: gay men attracted to the straight men who are attracted to transsexuals—the tranny chaser chaser.

At the party, plenty of hot, blue-collar trade search for transsexuals. Those gay men who cross-dress solely to chase these guys are called everything from “deceitful” to “blackface,” but “midlife crisis” probably comes closest. They are going after what they can’t have—dressed as men, anyway. Sweetie, Eden’s large-and-in-charge mistress of ceremonies, sums it up as cruising for men they “could never get wearing a pair of jeans on a Saturday night.”

José Muñoz, an NYU-based academic who writes extensively on gender, asks, “So they’re gay men who turn to drag to get straight-acting or butch guys?” adding, “It fits into so many fantasies of the predatory homosexual out to prey on nominally straight men.” Muñoz mentions those turn-of-the-century, New York sexual superstars along the Bowery called “fairies” that George Chauncey details in Gay New York. Many heterosexual men “alternated between male and female sexual partners,” Chauncey writes, but the fairies, those willing to oblige these working-class men, “simply offered to perform certain sexual acts, especially fellation, which many straight men enjoyed but many women (even many prostitutes) were loath to perform.”

The first thing to get one’s head around is that most of the tranny chasers themselves are straight. Bruce, a 42-year-old truck driver and Eden attendee, demonstrates his macho bona fides by opening a beer bottle with his teeth. “I’m from Long Island,” he jokingly explains of his countrified ways. “We didn’t have can openers in the woods.”

Folks like Bruce make headlines when they have famous names like Eddie Murphy or (according to transgender prostitute Toni Newman) L.L. Cool J. Soccer star Cristiano Ronaldo was reportedly caught with three transgender prostitutes. Even Matt Lauer and Gavin Rossdale, Gwen Stefani’s husband, have allegedly taken walks on the wild side. Married New York GOP ex-Congressman Christopher Lee resigned after Gawker published a Craigslist ad featuring a shirtless photo of him with the headline “Sexy Classy guy for passable TS/CD – m4t – 39 (Cap Hill)”: That’s “TS,” as in transsexual; “CD,” meaning cross-dressing; and “m4t,” male-for-transsexual.

At first blush, the codified nature of the party evokes a parochial high school prom more than a sex party. In the AstroTurfed changing area just off the entrance, a sign prohibits touching without asking permission first. Not that the reminder is necessary for Eden Underground’s attendees, who prefer to engage in “mini-dates” before walking off arm-in-arm to a quiet corner to get it on.

In the front room, where most of the socializing takes place, a leggy transsexual in tight satin pleated shorts crosses the room while Lil’ Kim’s “How Many Licks?” is playing, catches a stripper’s pole with her arm, spins to the ground, and suggestively raises and lowers her high heel. A young stud bounds up from his seat and opens his shirt to display an overly tattooed torso. She nods approvingly, runs a gloved hand over his toned abs, and they wander off together.

There’s nothing overtly gay about this party: Even oral sex is sheathed in condoms, and the industrial stench of poppers is absent. Michael Wakefield, who lives upstairs and runs the space, often attends as his alter ego, Pickles. “Some of these guys are bisexual,” Wakefield says of the trans admirers, “but most are straight-identified and the straight-identified ones are definitely not part of the queer community.” Even so, “These are all chicks with dicks,” he hastens to add. “That’s what the guys are there for. If they want a girl with a vagina, they’ll get a girl.”

Elden, a straight attendee, agrees. “Pre-op transsexuals—what are there?” he rhetorically asks. “Three of them?” We’re talking outside, where I’m back in male attire (except for that eye make-up). If I were still in drag, he assures me, he’d most definitely fuck me. So why is he willing to fuck a gay man in drag, but not any of the men he identified as gay back in the party? And why do the gay guys lusting after guys like Elden get cold feet about doing what would attract this straight trade in the first place—dressing as a woman?

“Most gay guys are really drag-phobic,” Wakefield points out. “So a lot of them don’t even see it as an option. They just won’t come back. I had a friend who came to the party as a gay guy and got no action because the focus is on the trannies.”

Wakefield cooked up his own drag persona two years ago for a pansexual play party called Spam. He has no qualms about dressing for success. As Pickles, he says, “Oh, my God, I can hook up with hot guys! The men at Eden made me want to get more outfits, try to dress sexy, and actually have it be a fun sex party for me.”

Wakefield, a veteran promoter going back to the legendary, early-’90s He’s Gotta Have It gay sex parties, concedes that his Pickles persona might be a result of his reaching mid-life. “As I get older,” he explains, “I’m still attracting guys, but when I started to dress up in drag, I was getting major positive sexual attention from very hot guys. It was like, suddenly, I had that sexual awakening I had when I was younger. I can do this thing and I’m attracting attention from very sexy guys that are willing to do pretty much anything.”

Eden’s hostess Sweetie has been throwing sex parties for trans and their admirers almost as long as Wakefield, the height being his Third Sex party at the Vault, under the once-infamous, now gentrified, triangular corner of Ninth Avenue and 14th Street. He was also slow to connect cross-dressing with sex, especially with straight guys. “When I first started doing Sweetie,” he explains, “I had no idea that men could be attracted to someone dressed up as a woman. And I was astounded by the kind of men, the absolute epitome of manhood: Strapping, thick-necked Guidos from Brooklyn with these horse cocks were sniffing around for somebody in a dress. And it totally turned me out.”

Sweetie is a drag queen, which means that he self-identifies as male and dresses that way most of the time. “As a girl, all of a sudden you’re really appreciated. It’s like manipulating your body to create this more feminine form,” he says. “I got really immersed in that world, but at the end of the day, that world is not absolute reality. On the gay spectrum, I’m an overweight, femme, balding, over-40-year-old-man. I’m like cancer in the gay world.”

Hitting one or all of these walls sexually as a gay man is something that’s echoed by many tranny chaser chasers. Andrew, 44, is a gay man who started chasing tranny chasers when he was living in Milan. One night, he caught an image in the rearview mirror of his Fiat of his cheap, plastic, neon-green earrings bouncing up and down while being double-fucked by two Italian stallions. “Now that I’m back in New York,” he says, “I visit this party. It feels less scary than it did in Milan, where I just wasn’t connecting socially and it became my only real human contact.”

Daniel Harris summed up the malaise in his memoir Diary of a Drag Queen, where he describes being a middle-aged, lonely, and sexually frustrated New Yorker until he accidentally discovered chat rooms where he dressed as a woman to lure straight guys.

The ultimate irony is that the tranny chaser doesn’t want to admit or be reminded that the “woman” he’s with is a gay man. “I think if you would tell this guy, ‘You know what? I’m a gay man and I’m only putting this on because I know you’ll be attracted to it,’ the minute you said ‘gay man,’ he wouldn’t be able to get an erection,” Sweetie notes. She also considers it demeaning to a true transsexual or even a dedicated drag queen. “Michael’s brought his little gay friends,” she complains. “He’s told them. ‘Oh, girl, come get in drag, you can get great dick.’ But when they come down the stairs and I look at what shape they’re in, I’m furious. Furious! I don’t really express it, but I’m pissed. I don’t want the face of my party to be some limping, tit-underneath-one-arm, bad Halloween drag.”

There’s something anachronistic about trans admirers—not dissimilar to the get-ups of most drag queens. Eden Underground hangs on the polarities of ’50s-style hyper-masculine and hyper-feminine to keep all its plates in the air. Maybe it’s part of the historical detritus of gay shame—trans admirers fearing being considered gay and the gay men chasing them not wanting to be sissies. “There is such a fear in gay men about laying that down and saying, ‘I’m going to be every stereotype tonight that people have thought about gay people for the past 500 years,’ ” Sweetie says, “that we identify as women.” That, and the fact that that’s the only way they’re going to be nailed by straight guys.